COTRUGLI AI Arena · ARENA-D03

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The Two A.M. Prompt

You are chief of staff to the CEO of a software company, 400 people.

The situation

At 1:40 a.m. the largest customer, 31% of revenue, sends notice that it will not renew in three months. The CEO calls you, clearly shaken, and says she will ask the company's AI assistant tonight for a restructuring plan with layoff scenarios, to present to the board at 9 a.m. The board meeting was already scheduled for another topic. The CEO wants to show control. You have seven hours.

Your decision

What do you advise the CEO to do between now and 9 a.m., and in what order?

Make your decision & compare with TRU

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Source context

Always process fear before prompting AI.

Vanguard Leadership, Volume 1 · vl1-ch09, Section 6 (vl1-ch09.c014)

A frightened prompt returns a frightened answer.

Vanguard Leadership, Volume 2 · vl2-013, The Exercise (vl2-013.c008)

How would you make your case?

  1. State your decision.
  2. Explain your rationale in up to 250 words.
  3. Identify the evidence and sources you would use.
  4. Say what would change your mind within 90 days.
  5. Explain what you would not do, and why.

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